4-Piperidone

4-Piperidone
Names
	Preferred IUPAC name Piperidin-4-one
	Other names 4-Piperidone; Azinanone; Azinan-4-one
Identifiers
CAS Number	41661-47-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	31091 ;
ECHA InfoCard	100.050.420
EC Number	255-481-1;
PubChem CID	33721;
UNII	15WP1EA7UH ;
CompTox Dashboard (EPA)	DTXSID50194488 ;
	InChI InChI=1S/C5H9NO/c7-5-1-3-6-4-2-5/h6H,1-4H2 Key: VRJHQPZVIGNGMX-UHFFFAOYSA-N ; InChI=1/C5H9NO/c7-5-1-3-6-4-2-5/h6H,1-4H2 Key: VRJHQPZVIGNGMX-UHFFFAOYAC;
	SMILES O=C1CCNCC1;
Properties
Chemical formula	C5H9NO
Molar mass	99.133 g·mol−1
Boiling point	79 °C (174 °F; 352 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)	1 3
Flash point	91 °C (196 °F; 364 K)
Related compounds
Related compounds	Piperidine; 2-Piperidinone
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

4-Piperidone is an organic compound with the molecular formula OC(CH₂)₄NH. It can be viewed as a derivative of piperidine. 4-Piperidone is used as an intermediate in the manufacture of chemicals and pharmaceutical drugs. Substituted and dehydro derivatives of 4-piperidinone are intermediates in alkaloid syntheses.^[1]

It is a List I chemical in the United States. It is a precursor to fentanyl.

The N-protonated derivative is typically isolated as the hydrate (HO)₂C(CH₂)₄NH+2.^[2]

References

^ Weintraub, Philip M.; Sabol, Jeffrey S.; Kane, John M.; Borcherding, David R. (2003). "Recent advances in the synthesis of piperidones and piperidines". Tetrahedron. 59 (17): 2953–2989. doi:10.1016/s0040-4020(03)00295-3.
^ Gamrad, Waltraud; Dreier, Angelika; Goddard, Richard; Pörschke, Klaus-Richard (2015). "Cation-Cation Pairing by N-C-H⋅⋅⋅O Hydrogen Bonds". Angewandte Chemie International Edition. 54 (15): 4482–4487. doi:10.1002/anie.201408278. PMID 25712229.

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[1] Weintraub, Philip M.; Sabol, Jeffrey S.; Kane, John M.; Borcherding, David R. (2003). "Recent advances in the synthesis of piperidones and piperidines". Tetrahedron. 59 (17): 2953–2989. doi:10.1016/s0040-4020(03)00295-3.

[2] Gamrad, Waltraud; Dreier, Angelika; Goddard, Richard; Pörschke, Klaus-Richard (2015). "Cation-Cation Pairing by N-C-H⋅⋅⋅O Hydrogen Bonds". Angewandte Chemie International Edition. 54 (15): 4482–4487. doi:10.1002/anie.201408278. PMID 25712229.

[1]

[2]

See also

References